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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-04-04 16:08:42 UTC
Update Date2022-09-22 17:44:16 UTC
HMDB IDHMDB0240340
Secondary Accession NumbersNone
Metabolite Identification
Common NameN-Acetyl-1-methylhistidine
DescriptionN-Acetyl-1-methylhistidine belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing histidine or a derivative thereof resulting from a reaction of histidine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. N-Acetyl-1-methylhistidine is an acetylated derivative of 1-methylhistidine and a very strong basic compound (based on its pKa). It has been found to be associated with chronic kidney disease: the higher the N-acetyl-1-methylhistidine levels, the lower the estimated glomerular filtration rate. This could make N-acetyl-1-methylhistidine a biomarker for chronic kidney disease (PMID: 24625756 ).
Structure
Data?1588018618
Synonyms
ValueSource
N-Acetyl-1-methylhistidineChEBI
Chemical FormulaC9H13N3O3
Average Molecular Weight211.221
Monoisotopic Molecular Weight211.095691291
IUPAC Name(2S)-2-acetamido-3-(1-methyl-1H-imidazol-4-yl)propanoic acid
Traditional Name(2S)-2-acetamido-3-(1-methylimidazol-4-yl)propanoic acid
CAS Registry Number84285-33-6
SMILES
CN1C=NC(C[C@H](NC(C)=O)C(O)=O)=C1
InChI Identifier
InChI=1S/C9H13N3O3/c1-6(13)11-8(9(14)15)3-7-4-12(2)5-10-7/h4-5,8H,3H2,1-2H3,(H,11,13)(H,14,15)/t8-/m0/s1
InChI KeyGVRCKHXHWSYDEF-QMMMGPOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as histidine and derivatives. Histidine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHistidine and derivatives
Alternative Parents
Substituents
  • Histidine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Imidazolyl carboxylic acid derivative
  • N-substituted imidazole
  • Azole
  • Imidazole
  • Acetamide
  • Heteroaromatic compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-0.55ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.62ChemAxon
pKa (Strongest Basic)6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.22 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.83 m³·mol⁻¹ChemAxon
Polarizability21.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+148.41730932474
DeepCCS[M-H]-146.02230932474
DeepCCS[M-2H]-179.02330932474
DeepCCS[M+Na]+154.4230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Acetyl-1-methylhistidineCN1C=NC(C[C@H](NC(C)=O)C(O)=O)=C13066.1Standard polar33892256
N-Acetyl-1-methylhistidineCN1C=NC(C[C@H](NC(C)=O)C(O)=O)=C11904.5Standard non polar33892256
N-Acetyl-1-methylhistidineCN1C=NC(C[C@H](NC(C)=O)C(O)=O)=C11986.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Acetyl-1-methylhistidine,1TMS,isomer #1CC(=O)N[C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C1999.6Semi standard non polar33892256
N-Acetyl-1-methylhistidine,1TMS,isomer #2CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O)[Si](C)(C)C1987.3Semi standard non polar33892256
N-Acetyl-1-methylhistidine,2TMS,isomer #1CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C1998.5Semi standard non polar33892256
N-Acetyl-1-methylhistidine,2TMS,isomer #1CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2002.7Standard non polar33892256
N-Acetyl-1-methylhistidine,2TMS,isomer #1CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C)[Si](C)(C)C2514.5Standard polar33892256
N-Acetyl-1-methylhistidine,1TBDMS,isomer #1CC(=O)N[C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C2258.9Semi standard non polar33892256
N-Acetyl-1-methylhistidine,1TBDMS,isomer #2CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O)[Si](C)(C)C(C)(C)C2235.3Semi standard non polar33892256
N-Acetyl-1-methylhistidine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2465.8Semi standard non polar33892256
N-Acetyl-1-methylhistidine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2438.8Standard non polar33892256
N-Acetyl-1-methylhistidine,2TBDMS,isomer #1CC(=O)N([C@@H](CC1=CN(C)C=N1)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2678.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-1-methylhistidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Acetyl-1-methylhistidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-1-methylhistidine 10V, Negative-QTOFsplash10-03xr-0690000000-ed7db8a2d71947e9b2582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-1-methylhistidine 20V, Negative-QTOFsplash10-0230-3920000000-ac6021b5e12f1772dd232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-1-methylhistidine 40V, Negative-QTOFsplash10-001l-9300000000-fb89cca2bedb842c84992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-1-methylhistidine 10V, Positive-QTOFsplash10-03dl-0590000000-5231dd89289b7d57c9a42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-1-methylhistidine 20V, Positive-QTOFsplash10-0fka-2900000000-aeb8e308c126dfb904cf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Acetyl-1-methylhistidine 40V, Positive-QTOFsplash10-0kmj-8900000000-250f128d2764bdfa35e22021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (40 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedElderly (>65 years old)MaleRenal failure with dialysis details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID57560763
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53859791
PDB IDNot Available
ChEBI ID133181
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yu B, Zheng Y, Alexander D, Morrison AC, Coresh J, Boerwinkle E: Genetic determinants influencing human serum metabolome among African Americans. PLoS Genet. 2014 Mar 13;10(3):e1004212. doi: 10.1371/journal.pgen.1004212. eCollection 2014 Mar. [PubMed:24625756 ]